# US 11,999,726 B2 · 5-methyl-4-fluoro-thiazol-2-yl compounds

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- Number: US 11,999,726 B2
- Document ID: US11999726B2
- Status: Granted
- Kind: B2
- Application number: 17/259,993
- Filed: 2019-07-24
- Published: 2021-10-21
- Granted: 2024-06-04
- Earliest claimed: 2018-07-31
- Applicants: Eli Lilly and Company
- Inventors: Nicolas Jacques Francois Dreyfus; Peter James Lindsay-Scott
- Web page: https://patentgrep.com/patent/US11999726B2

## CPC

- C07D 417/14: containing three or more hetero rings
- A61P 25/00: Drugs for disorders of the nervous system
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides a compound of Formula I: or a pharmaceutically acceptable salt thereof, and the use of compounds of Formula I for treating neurodegenerative diseases, such as Alzheimers disease.

## Claims

### Claim 1

A compound of the formula;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound according to claim 1 wherein the methyl at position 2 on the piperidine ring is in the cis configuration relative to the oxygen at position 4:
or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

The compound according to claim 1 wherein the compound is:
or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 3)

The compound according to claim 3 wherein the compound is:

### Claim 5 (depends on 4)

The compound according to claim 4 which is crystalline.

### Claim 6 (depends on 5)

The compound according to claim 5 which is characterized by a peak in the X-ray diffraction spectrum, at diffraction angle 2-theta of 12.1° in combination with one or more of the peaks selected from the group consisting of 18.5°, 13.0°, and 16.0°, with a tolerance for the diffraction angles of 0.2 degrees.

### Claim 7 (depends on 1)

A method of treating Alzheimer's disease in a patient, comprising administering to a patient in need of such treatment an effective amount of a compound of claim 1, or a pharmaceutically acceptable salt thereof.

### Claim 8 (depends on 1)

A method of treating the progression of mild cognitive impairment to Alzheimer's disease in a patient, comprising administering to a patient in need of such treatment an effective amount of a compound of claim 1, or a pharmaceutically acceptable salt thereof.

### Claim 9 (depends on 1)

A method of treating progressive supranuclear palsy in a patient, comprising administering to a patient in need of such treatment an effective amount of a compound of claim 1, or a pharmaceutically acceptable salt thereof.

### Claim 10 (depends on 1)

A pharmaceutical composition, comprising a compound or a pharmaceutically acceptable salt thereof according to claim 1, with one or more pharmaceutically acceptable carriers, diluents, or excipients.

### Claim 11 (depends on 1)

A process for preparing a pharmaceutical composition, comprising admixing a compound or a pharmaceutically acceptable salt thereof according to claim 1 with one or more pharmaceutically acceptable carriers, diluents, or excipients.